I kept "optimizing" my writing stack… until I realized the real bottleneck was context switching

Hey IH 👋

For the last couple of years I’ve been building small tools and shipping a lot of writing alongside them: landing pages, docs, changelogs, support replies, outreach, investor updates… basically anything that turns “a thing I built” into “a thing someone understands.”

If you’ve built products, you know the deal: the writing never ends.

And because the writing never ends, I did what builders do best — I started optimizing the stack.

Better editor
Better templates
Better prompts
Better frameworks for copy
Better “voice” guidelines
Better everything

It helped… but not in the way I expected.

Because the problem wasn’t my writing ability.
It wasn’t even the tools.

It was the way the tools fit into my flow.

The pattern I kept repeating

This is embarrassing, but here’s what a normal “tighten this paragraph” loop looked like for me:

Draft something quickly
Hit a sentence that sounds off
Copy it
Jump to another tab/tool
Paste
Wait
Read 3–5 options
Copy the best one
Jump back
Paste
Fix formatting
Re-read the paragraph to remember what I was doing

That loop doesn’t feel expensive once.

It becomes expensive when it happens 30–100 times in one piece of writing. And it happens more often than you think, because rewriting is basically the whole job after “draft.”

At some point I realized I wasn’t losing time on writing.

I was losing time on re-entering writing.

The moment it clicked (it wasn’t “AI quality”)

I used to blame output quality.

Like: “Maybe I just need better prompts.”
Or: “Maybe I need a tool that’s a bit smarter.”
Or: “Maybe I need a more structured writing system.”

But then I noticed something: even when the rewrite was great, I still felt slightly irritated and mentally scattered after doing it.

So I started paying attention to the feeling.

Every time I left the doc, my brain did a tiny reset:

I lost the sentence rhythm
I lost the paragraph direction
I lost the tone
I lost the motivation to keep going

This is the same thing engineers complain about when they get pulled into meetings: the real cost isn’t the meeting, it’s the context reload after.

Writing has the same tax. And the tax is brutal because writing is fragile.

It reminded me of a dev lesson I learned the hard way

Early on, I shipped a feature that was “technically correct” but painful to use.

It required the user to:

navigate to a separate screen
configure something
confirm it
go back
repeat

Power users could do it. But nobody wanted to.

So we moved the action closer to where the user already was:

same screen
fewer steps
instant feedback

Adoption jumped.

That’s when it hit me: my writing workflow had the same UX problem.

I didn’t need a smarter system.
I needed fewer steps between intention → execution.

The “small” change that made a huge difference

What I wanted was simple:

When I’m writing, and a sentence is almost right, I don’t want to:

open a new tab
paste
wait
come back

I want to rewrite where the sentence lives.

Same place.
Same context.
Same momentum.

That’s the entire idea that led to what I’m building now.

What I’m working on now

I’m building a tiny tool that makes rewriting feel like an editing shortcut instead of a separate workflow.

Not a “go to a dashboard” product.
More like: “stay in your doc and keep moving.”

If you’re curious, here it is: https://rephrazo-ai.app/

A question for IH

If you write a lot (docs, marketing, outreach, support):

What breaks your flow the most?

switching tools?
rewriting tone?
getting stuck on intros/hooks?
editing for brevity?
something else?

I’m collecting real workflows + pain points, because I don’t want to build another “AI tool” that’s powerful but annoying.

Would love to hear how you handle the rewrite loop.